Cheryl holds a Bachelor of Arts degree from McGill University, a graduate diploma in journalism from Concordia University, and a Bachelor of Laws degree from the University of Ottawa. While at the University of Ottawa, Cheryl was chosen to debate in the 2008 bilingual Laskin moot in constitutional and administrative law.

Before entering the legal field, Cheryl worked as an on-air political correspondent, an associate news producer for a national television network, and a senior researcher and story producer for several television documentary series.

Cheryl articled at a prominent Bay Street law firm, and was called to the Ontario Bar in June 2009.